Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment. Academic Article uri icon


  • Detailed computational (DFT) studies of the palladium(II)-catalyzed Claisen rearrangement of 2-allyloxy- and propargyloxyindoles revealed an unexpected divergent mode of reactivity. Subsequent experimental kinetic isotope effects are in accord with the mechanism derived from the computations. The computational results led to the development of Pd(II)-catalyzed [3,3]-sigmatropic rearrangement of 3-aryl substituted 2-propargylindoles.

published proceedings

  • Org Lett

author list (cited authors)

  • Gutierrez, O., Hendrick, C. E., & Kozlowski, M. C.

complete list of authors

  • Gutierrez, Osvaldo||Hendrick, Charles E||Kozlowski, Marisa C

publication date

  • October 2018